A lot of interesting comments here. Being 68 going on 69 myself, it's great to hear from so many that are about my age.
I too care less about what most others think as I get older and closer to meeting the grim reaper. However, my wife does care, a lot! So as long as she's around (and I expect her to outlast me based on standard probabilities) I am unable to 'come out' to anyone but her. So I go across town a few times a week, away from those that know us, and do the grocery shopping (and expand my female wardrobe). Not perfect, but you do what you can with what you have to work with.